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Combined dehydration/(transfer)-hydrogenation of C6-sugars (D-glucose and D-fructose) to gamma-valerolactone using ruthenium catalysts

Heeres, H., Handana, R., Chunai, D., Rasrendra, C. B., Girisuta, B. & Heeres, H. J., 2009, In : Green Chemistry. 11, 8, p. 1247-1255 9 p.

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  • Hans Heeres
  • Ratna Handana
  • Dai Chunai
  • Carolus Borromeus Rasrendra
  • Buana Girisuta
  • Hero Jan Heeres

gamma-Valerolactone (GVL) is considered a very interesting green, bio-based platform chemical with high application potential. We here describe research activities on the one-pot catalytic synthesis of GVL from C6-sugar sources (D-glucose, D-fructose, sucrose and cellulose) using an acid catalyst in combination with a hydrogenation catalyst (Ru/C) and either molecular hydrogen or formic acid as the hydrogen donor. When using formic acid, the highest yield of GVL (52 mol%) was obtained at 180 degrees C, 16 h reaction time and D-fructose as the C6-sugar source. The major by-products were insoluble solids, known as humins, formed during the acid catalysed conversion of D-fructose to the intermediate levulinic acid (LA). When using molecular hydrogen as the hydrogen source, the highest yield of GVL (62 mol%) was obtained using D-fructose in combination with TFA and Ru/C in water (180 degrees C, 94 bar H(2), 8 h). Complete conversion of D-fructose was observed at these conditions. The major by-products were formic acid and insoluble solid materials (humins). The use of a pre-formed homogeneous water soluble ruthenium catalysts from RuCl(3) and tris(3-sulfonatophenyl) phosphane (TPPTS) in combination with TFA gave quantitative C6-sugar conversions but a lower GVL yield (23 mol%) compared to the heterogeneous Ru catalyst.

Original languageEnglish
Pages (from-to)1247-1255
Number of pages9
JournalGreen Chemistry
Volume11
Issue number8
Publication statusPublished - 2009

    Keywords

  • LEVULINIC ACID, PHOSPHINE COMPLEXES, ORGANIC-ACIDS, BIOMASS, CONVERSION, HYDROGENATION, DEHYDRATION, CHEMISTRY, SORBITOL, WATER

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